On-Surface Dehydro-Diels-Alder Reaction of Dibromo-bis(phenylethynyl)benzene
Di Giovannantonio M, Keerthi A, Urgel JI, Baumgarten M, Feng X, Ruffieux P, Narita A, Fasel R, Muellen K (2020)
Publication Type: Journal article
Publication year: 2020
Journal
Book Volume: 142
Pages Range: 1721-1725
Journal Issue: 4
DOI: 10.1021/jacs.9b11755
Abstract
On-surface synthesis under ultrahigh vacuum conditions is a powerful tool to achieve molecular structures that cannot be accessed via traditional wet chemistry. Nevertheless, only a very limited number of chemical reactions out of the wide variety known from solution chemistry have been reported to proceed readily on atomically flat substrates. Cycloadditions are a class of reactions that are particularly important in the synthesis of sp2-hybridized carbon-based nanostructures. Here, we report on a specific type of [4 + 2] cycloaddition, namely, a dehydro-Diels-Alder (DDA) reaction, performed between bis(phenylethynyl)-benzene precursors on Au(111). Unlike a Diels-Alder reaction, DDA exploits ethynyl groups to achieve the formation of an extra six-membered ring. Despite its extensive use in solution chemistry for more than a century, this reaction has never been reported to occur on surfaces. The specific choice of our precursor molecule has led to the successful synthesis of benzo- A nd naphtho-fused tetracene and heptacene products bearing styryl groups, as confirmed by scanning tunneling microscopy and noncontact atomic force microscopy. The two products arise from dimerization and trimerization of the precursor molecules, respectively, and their observation opens perspectives to use DDA reactions as a novel on-surface synthesis tool.
Involved external institutions
Eidgenössische Materialprüfungs- und Forschungsanstalt (Empa) / Swiss Federal Laboratories for Materials Science & Technology
Switzerland (CH)
Max-Planck-Institut für Polymerforschung (MPI-P) / Max Planck Institute for Polymer Research
Germany (DE)
Technische Universität Dresden
Germany (DE)
Switzerland (CH)
Max-Planck-Institut für Polymerforschung (MPI-P) / Max Planck Institute for Polymer Research
Germany (DE)
Technische Universität Dresden
Germany (DE)
How to cite
APA:
Di Giovannantonio, M., Keerthi, A., Urgel, J.I., Baumgarten, M., Feng, X., Ruffieux, P.,... Muellen, K. (2020). On-Surface Dehydro-Diels-Alder Reaction of Dibromo-bis(phenylethynyl)benzene. Journal of the American Chemical Society, 142(4), 1721-1725. https://doi.org/10.1021/jacs.9b11755
MLA:
Di Giovannantonio, Marco, et al. "On-Surface Dehydro-Diels-Alder Reaction of Dibromo-bis(phenylethynyl)benzene." Journal of the American Chemical Society 142.4 (2020): 1721-1725.
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